Use of norbornyl ethers in augmenting or enhancing the aroma of perfumes and colognes

ABSTRACT

Described are the uses for augmenting or enhancing the aroma of perfume compositions and colognes of the compounds having the structures: ##STR1## wherein &#34;R&#34; represents isopropyl, phenethyl, allyl, cyclohexyl, hydroxyl alkyl or alkoxy alkyl.

This application is a continuation-in-part of application for UnitedStates Letters Patent Ser. No. 280,856 filed July 6, 1981, nowabandoned, which, in turn, is a streamline divisional of application forUnited States Letters Patent Ser. No. 200,012 filed on Oct. 23, 1980,now U.S. Pat. No. 4,311,861 issued on Jan. 19, 1982.

BACKGROUND OF THE INVENTION

The present invention relates to substituted norbornene etherderivatives of the genus of compounds having the structures: ##STR2##wherein R represents C₃ -C₆ alkyl; aralkyl; hydroxy alkyl; and alkoxyalkyl, and uses thereof in order to alter, modify or enhance the aromaof consumable materials.

There has been considerable work performed relating to substances whichcan be used to impart (modify, augment or enhance) fragrances to (or in)various consumable materials. These substances are used to diminish theuse of natural materials, some of which may be in short supply and toprovide more uniform properties in the finished product.

Long-lasting, fresh, green bean, rosey, citrus, petitgrain-like, fruity,anisic, green, raw potato-like, twiggy, herbaceous, sweet, sweaty, greenpea-like, chocolate-like, carrot-like and creamy aroma nuances withgalbanum topnotes and anther-like and anise-like undertones aredesirable in several types of perfume compositions, perfumed articlesand colognes.

The perfume use of norbornene alcohol and ester derivatives having thestructures: ##STR3## wherein R₁ is C₁ -C₄ alkyl is disclosed in U.S.Pat. No. 3,860,635 particularly at Example XV at column 16 thereof. Suchcompounds and the synthesis thereof are also disclosed by Bobyleva, Zh.Org. Kh. Volume 13, No. 10, pages 2085-92, October 1977. In addition,ethers of norbornene derivatives having the structures: ##STR4## aredisclosed as well as the process for preparing same according to thereaction: ##STR5## in Shield, Can. J. Chem. Volume 49, 1971, page 1142.

U.S. Pat. No. 3,927,116 indicates the utility of certain vinyl norbornylethers having the structure: ##STR6## wherein R₂ represents C₁ -C₄ alkylas being intermediate for the preparation of detergents at column 9lines 10-15.

The compounds of our invention, having the structures: ##STR7## haveunobvious, unexpected and advantageous perfumery properties over anyclosely similar compounds of the prior art.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 sets forth the GLC profile for the crude reaction product ofExample I containing the compounds having the structures: ##STR8##

FIG. 1(A) is the GLC profile of the purified reaction product of ExampleI containing the compounds having the structures: ##STR9## wherein peak2 on said FIG. 1(A) is the compound having the structure: ##STR10## andpeak 3 on said FIG. 1(A) consists of the compound having the structure:##STR11##

FIG. 2 sets forth the NMR spectrum for the reaction product of Example1(A) containing the compounds having the structures: ##STR12##

FIG. 2(A) represents the NMR spectrum for peak 2 of the GLC profile ofFIG. 1(A) and consists of the compound having the structure: ##STR13##

FIG. 2(B) is the NMR spectrum for peak 3 of the GLC profile of FIG. 1(A)and consists essentially of the compound having the structure: ##STR14##

FIG. 3 sets forth the infra red spectrum for the reaction product ofExample I containing the compounds having the structures: ##STR15##

FIG. 3(A) represents the infra red spectrum for peak 2 of the GLCprofile of FIG. 1(A) which peak consists essentially of the compoundhaving the structure: ##STR16##

FIG. 3(B) represents the infra red spectrum for peak 3 of the GLCprofile of FIG. 1(A) and consists essentially of the compound having thestructure: ##STR17##

FIG. 4 sets forth the GLC profile for the reaction product of Example IIcontaining the compounds having the structures: ##STR18##

FIG. 5 sets forth the NMR spectrum for the reaction product of ExampleII containing the compounds having the structures: ##STR19##

FIG. 6 is the infra red spectrum for the reaction product of Example IIcontaining the compounds having the structures: ##STR20##

FIG. 7 sets for the GLC profile for the reaction product of Example IIIcontaining the compounds having the structures: ##STR21##

FIG. 8 represents the NMR spectrum for the reaction product of ExampleIII containing the compounds having the structures: ##STR22##

FIG. 9 sets forth the infra red spectrum for the reaction product ofExample III containing the compounds having the structures: ##STR23##

FIG. 10 represents the GLC profile for the reaction product of ExampleIV containing the compounds having the structures: ##STR24##

FIG. 11 sets forth the NMR spectrum for the reaction product of ExampleIV containing the compounds having the structures: ##STR25##

FIG. 12 represents the infra red spectrum for the reaction product ofExample IV containing the compounds having the structures: ##STR26##

FIG. 13 is the NMR spectrum for the reaction product of Example Vcontaining the compounds having the structures: ##STR27##

FIG. 14 sets forth the infra red spectrum for the reaction product ofExample V containing the compounds having the structures: ##STR28##

FIG. 15 represents the GLC profile for the reaction product of ExampleVI containing the compounds having the structures: ##STR29##

FIG. 16 sets forth the NMR spectrum for the reaction product of ExampleVI containing the compounds having the structures: ##STR30##

FIG. 17 represents the infra red spectrum for the reaction product ofExample VI containing the compounds having the structures: ##STR31##

FIG. 18 sets forth the GLC profile for the reaction product of ExampleVII containing the compounds having the structures: ##STR32##

FIG. 19 sets forth the NMR spectrum for the reaction product of ExampleVII containing the compounds having the structures: ##STR33##

FIG. 20 sets forth the infra red spectrum for the reaction product ofExample VII containing the compounds having the structures: ##STR34##

FIG. 21 sets forth the GLC profile for the reaction product of ExampleVIII containing the compounds having the structures: ##STR35##

FIG. 22 sets forth the NMR spectrum for the reaction product of ExampleVIII containing the compounds having the structures ##STR36##

FIG. 23 sets forth the infra red spectrum for the reaction product ofExample VIII containing the compounds having the structures: ##STR37##

FIG. 24 sets forth the GLC profile for the reaction product of ExampleIX containing the compounds having the structures: ##STR38##

FIG. 25 sets forth the NMR spectrum for the reaction product of ExampleIX containing the compounds having the structures: ##STR39##

FIG. 26 sets forth the infra red spectrum for the reaction product ofExample IX containing the compounds having the structures: ##STR40##

FIG. 27 sets forth the GLC profile for the reaction product of Example Xcontaining the compounds having the structures: ##STR41##

FIG. 28 sets forth the NMR spectrum for the reaction product of ExampleX containing the compounds having the structures: ##STR42##

FIG. 29 sets forth the infra red spectrum for the reaction product ofExample X containing the compounds having the structures: ##STR43##

FIG. 30 sets forth the GLC profile for the reaction product of ExampleXI containing the compounds having the structures: ##STR44##

FIG. 31 sets forth the NMR spectrum for the reaction product of ExampleXI containing the compounds having the structures: ##STR45##

FIG. 32 sets forth the infra red spectrum for the reaction product ofExample XI containing the compounds having the structures: ##STR46##

DETAILED DESCRIPTION OF THE DRAWINGS

FIG. 1(A) is the GLC profile for the reaction product produced accordingto Example I and contains starting material having the structure:##STR47## as well as reaction products: ##STR48## Reference "1"indicates the peak of this GLC profile which consists of the compoundhaving the structure: ##STR49## Reference "2" indicates the peak of theGLC profile which consists essentially of the compound having thestructure: ##STR50## Reference "3" indicates the peak of the GLC profilewhich consists essentially of the compound having the structure:##STR51##

The instant invention relates to the use for augmenting or enhancing thearoma of perfumes, perfumed articles and colognes of compounds havingthe generic structures: ##STR52## either taken alone or in admixturewherein R represents C₃ -C₆ alkyl; aralkyl; hydroxy alkyl; and alkoxyalkyl.

These compounds as a group have long lasting, fresh, green bean, rosey,citrus, petitgrain-like, fruity, anisic, green, raw potato-like, twiggy,herbaceous, sweet, sweaty, green pea-like, chocolate-like, carrot-likeand creamy aroma nuances with galbanum topnotes and anther-like andanise-like undertones.

The compounds of our invention may be prepared by reacting ethylidenenorbornene having the structure: ##STR53## with ROH, and alcohol whereinR represents C₃ -C₆ alkyl; aralkyl; hydroxy alkyl; and alkoxy alkyl inthe presence of a catalyst which is either a mineral acid or a Lewisacid. Examples of mineral acid catalysts are sulfuric acid, phosphoricacid, para-toluene sulfonic acid, methane sulfonic acid and acidionexchange resin. Examples of Lewis acid which can be use as catalystsare boron trifluoride etherate, aluminum chloride, zinc chloride,stannic chloride, stannouse chloride, zinc bromide, diethyl aluminumchloride, ethyl aluminum dichloride, ethyl aluminum dibromide anddiethyl aluminum bromide. The reaction preferably takes place in thepresence of an inert sorvent such as tetrahydrofuran, toluene orbenzene. The reaction may take place in the absence of the inert solventand in the presence of an excess of the alcohol reactant, the excess ofthe alcohol reactant being used as the "solvent".

The reaction temperature may vary from about 25° C. up to 120° C. withreflux temperature being preferred. The reflux temperature depends uponthe pressure in the reactor and the particular solvent being used aswell as its concentration. The mole ratio of acid catalyst to ethylidenenorbornene may vary from about 1:99 up to about 1:10. The mole ratio ofethylidene norbornene reactant to ROH alcohol reactant may vary fromabout 1:1 up to about 1:2 with a mole ratio of 1:1.5 of norbornene:alcohol reactant being preferred. Thus, the reaction to produce thecompounds of our invention may be shown thusly: ##STR54##

The compounds of our invention are usually prepared in admixture withcompounds having the generic structure: ##STR55## being prepared alongwith compounds having the structure: ##STR56## These compounds, however,may be separated by distillation, extraction and preparative GLCtechniques in order to yield separately compounds having the structure:##STR57## and separate therefrom compounds having the structure:##STR58##

In addition, the compounds having the structure: ##STR59## exist inisomeric forms and are produced in admixture. The mixture of these"endo" and "exo" and "cis" and "trans" isomers may be separated from oneanother by means of standard separation techniques including preparativeGLC techniques whereby the individual isomers may be separated and thenutilized individually. Structures of these isomers are as follows:##STR60##

Specific examples of the compounds produced according to the foregoingprocess and useful for the practice of my invention are set forth intable I below.

                  TABLE I                                                         ______________________________________                                        Structure of Compounds                                                                           Perfumery Evaluation                                       ______________________________________                                         ##STR61##         A fresh, green bean-like rosey, citrus, (petitgrain-                          like) aroma.                                               and                                                                            ##STR62##                                                                    Produced according to                                                         Example I                                                                      ##STR63##         A fruity, anisic, green aroma.                             and                                                                            ##STR64##                                                                    Produced according to                                                         Example II                                                                     ##STR65##         A green, raw potato aroma with galbanum topnotes.          and                                                                            ##STR66##                                                                    Produced according to                                                         Example III                                                                    ##STR67##         A long lasting, green,  twiggy, fruity and herbaceous                         aroma.                                                     and                                                                            ##STR68##                                                                    Produced according to                                                         Example IV                                                                     ##STR69##         A sweet, fruity aroma.                                     and                                                                            ##STR70##                                                                    Produced according to                                                         Example V                                                                      ##STR71##         An excellent green aroma.                                  and                                                                            ##STR72##                                                                    Produced according to                                                         Example VI                                                                     ##STR73##         A green, sweaty aroma.                                     and                                                                            ##STR74##                                                                    Produced according to                                                         Example VII                                                                    ##STR75##         A green pea-like and green aroma.                          and                                                                            ##STR76##                                                                    Produced according to                                                         Example VIII                                                                   ##STR77##         A green and chocolate-like aroma with anther-like                             undertones                                                  ##STR78##                                                                    Produced according to                                                         Example IX                                                                     ##STR79##         A floral, green and carrot-like aroma.                     and                                                                            ##STR80##                                                                    Produced according to                                                         Example X                                                                      ##STR81##         A green, creamy, string- bean-like, herbaceous and                            floral-rosey aroma with anise-like under- tones.           and                                                                            ##STR82##                                                                    Produced according to                                                         Example XI                                                                    ______________________________________                                    

The norbornyl ether derivative(s) and one or more auxiliary perfumeingredients, including, for example, hydrocarbons, alcohols, ketones,aldehydes, nitriles, esters, lactones, ethers other than said norbornylether derivative(s), hydrocarbons, synthetic essential oils and naturalessential oils may be admixed so that the combined odors of theindividual components produce a pleasant and desired fragrance,particularly and preferably in citrusy and/or green woody and/or pineyfragrances. Such perfume compositions usually contain (a) the main noteor the "bouquet" or foundation stone of the composition; (b) modifierswhich round off and accompany the main note; (c) fixatives which includeodorous substances which lend a particular note to the perfumethroughout all stages of evaporation and substances which retardevaporation; and (d) topnotes which are usually low boiling freshsmelling materials.

In perfume compositions, it is the individual components whichcontribute to their particular olfactory characteristics, however theover-all sensory effect of the perfume composition will be at least thesum total of the effects of each of the ingredients. Thus, one or moreof the norbornyl ether derivative(s) of our invention can be used toalter, modify or enhance the aroma characteristic of a perfumecomposition, for example, by utilizing or moderating the olfactoryreaction contributed by another ingredient in the composition.

The amount of norbornyl ether derivative(s) of our invention which willbe effective in perfume compositions as well as in perfumed articles andcolognes depends upon many factors, including the other ingredients,their amounts and the effects which are desired. It has been found thatperfume compositions containing as little as 0.005% of norbornyl etherderivative(s) or even less (e.g. 0.002%) can be used to impart fresh,green bean, rosey, citrus, petitgrain-like, fruity, anisic, green, rawpotato-like, twiggy, herbaceous, sweet, sweaty, green pea-like,chocolate-like, floral, carrot-like and creamy aroma nuances withgalbanum topnotes and anther-like and anise-like undertones to soaps,cosmetics, detergents (including anionic, non-ionic, zwitterionic andcationic solid or liquid detergents) or other products. The amountemployed can range up to 70% of the fragrance components and will dependupon considerations of cost, nature of the end product, the effectdesired on the finished product and the particular fragrance sought.

The norbornyl ether derivative(s) of our invention are useful (takenalone or together with other detergents in perfume compositions) indetergents and soaps, space odorants and deodorants, perfumes, colognes,toilet water, bath preparations such as lacquers brilliantines, pomadesand shampoos; cosmetic preparations, such as creams, deodorants, handlotions and sun screens; powders such as talcs, dusting powders, facepowders and the like. As little as 0.25% of the norbornyl etherderivative(s) will suffice to impart an intense green, petitgrain-like,rosey and citrusy notes to citrusy, woody, floral and piney perfumeformulations. Generally, no more than 5% of the norbonyl etherderivative(s) based on the ultimate end product is required to be usedas is or in the perfume composition.

Furthermore, as little as 0.25% of the norbornyl ether derivative(s)will suffice to impart such aroma to perfumed articles per se, whetherin the presence of other perfume materials or whether used by itself.Thus, the range of use of the norbornyl ether derivative(s) of ourinvention in perfumed articles may vary from 0.25% up to 5% by weightbased on the total weight of the perfumed article.

In addition, the perfume composition or fragrance composition of ourinvention can contain a vehicle, or carrier for the norbornyl etherderivative(s). The vehicle can be a liquid such as a non-toxic alcohol,e.g. ethanol, a non-toxic glycol, e.g. propylene glycol or the like. Thecarrier can also be an absorbent solid, such as a gum, (e.g. gumarabic), or components for encapsulating the composition by means ofcoacervation (such as gelatin).

It will thus be apparent that the norbornyl ether derivative(s) of ourinvention can be utilized to alter, modify or enhance aroma of perfumecompositions, colognes or perfumed articles.

Examples I-XI, following, serve to illustrate processes for specificallyproducing the norbornyl ether derivative(s) useful in our invention.

The following examples in general, serve to illustrate specificembodiments of our invention. It will be understood that these examplesare illustrative and the invention is to be considered restrictedthereto only as indicated in the appended claims. All parts andpercentages given herewith are by weight unless otherwise specified.

EXAMPLE I PREPARATION OF A MIXTURE OF2-ETHYL-5-ISOPROPYLTRICYCLO[2.2.1.0.sup.(2,6) ]HEPTANE and2-ETHYLIDENE-6-ISOPROPOXYNORBORNANE ##STR83##

Vinylidene norbornene (480 grams) is added over a 90 minute period to astirred solution of isopropanol (300 grams) and boron trifluorideetherate (12 grams) at reflux (temperature varies from 75° C. to 97°C.). The reaction mass is quenched with 1 liter of water. The organiclayer is subsequently washed with 500 ml of 10% NaOH. Distillationthrough a 11/2"×12" Goodloe® packed column affords 651 grams of product(b.p. 75° C. at 5 mmHg pressure).

FIG. 1 sets forth the GLC profile for the crude reaction product ofExample I containing the compounds having the structures: ##STR84##

FIG. 1(A) is the GLC profile of the purified reaction product of ExampleI containing the compounds having the structures: ##STR85## wherein peak2 on said FIG. 1(A) is the compound having the structure: ##STR86## andpeak 3 on said FIG. 1(A) consists of the compound having the structure:##STR87##

FIG. 2 sets forth the NMR spectrum of the product mixture consisting of2-ethyl-5-isopropyltricyclo[2.2.1.0.sup.(2,6) ]heptane and2-ethylidene-6-isopropoxynorbornane having respectively, the structures:##STR88##

FIG. 2(A) sets forth the NMR spectrum for peak 2 of the GLC profile ofFIG. 1(A) consisting of the compound having the structure: ##STR89##

FIG. 2(B) sets forth the NMR spectrum for peak 3 of the GLC profile ofFIG. 1(A) consisting of the compound having the structure: ##STR90##

FIG. 3 sets forth the infra red spectrum of the product mixtureconsisting of 2-ethyl-5-isopropyltricyclo[2.2.1.0.sup.(2,6) ]heptane and2-ethylidene-6-isopropoxynorbornane.

FIG. 3(A) sets forth the infra red spectrum for peak 2 of the GLCprofile of FIG. 1(A) consisting of the compound having the structure:##STR91##

FIG. 3(B) sets forth the infra red spectrum for peak 3 of the GLCprofile of FIG. 1(A) consisting of the compound having the structure:##STR92##

EXAMPLE II PREPARATION OF A MIXTURE CONSISTING OF2-ETHYL-5-ALLYLTRICYCLO[2.2.1.0.sup.(2,6) ]HEPTANE and2-ETHYLIDENE-6-ALLYLNORBORNANE ##STR93##

Ethylidene norbornene (480 grams) is added over a 90 minute period to astirred solution of toluene (250 ml), allyl alcohol (267 grams), and BF₃etherate (15 ml) at reflux. The reaction mass is quenched with 1 literof water and the organic layer is washed with 500 ml of 10% sodiumcarbonate. The toluene is removed on a rotary evaporator. The organicsolution is distilled through a 11/2"×12" Goodloe® packed column toafford 490 grams of product (b.p. 60° C. at 3 mmHg pressure).

FIG. 4 represents the GLC profile of the crude product (conditions: 150°C. isothermal, 10'×1/4", 10% SE-30 packed column).

FIG. 5 shows the NRM spectrum of the mixture consisting of2-ethyl-5-allyltricyclo[2.2.1.0.sup.(2,6) ]heptane and2-ethylidene-6-allylnorbornane, respectively having the structures:##STR94##

FIG. 6 sets forth the infra red spectrum of the mixture consisting of2-ethyl-5-allyltricyclo[2.2.1.0.sup.(2,6) ]heptane and2-ethylidene-6-allylnorbornane.

EXAMPLE III PREPARATION OF A MIXTURE CONSISTING OF2-ETHYL-5-(β-HYDROXYETHOXY)-TRICYCLO[2.2.1.0.sup.(2,6) ]HEPTANE and2-ETHYLIDENE-6-(β-HYDROXYETHOXY)-NORBORNANE ##STR95##

Ethylidene norbornene (480 grams) is added over a 41/2 hour period to astirred solution of ethylene glycol (186 grams) and boron trifluorideetherate (15 ml) at 60° C. At the end of this period the resultingorganic reaction mass is washed two times with 500 ml of water andwashed once with 500 ml of 10% sodium carbonate solution.

The resulting organic layer is then distilled through a 11/2"×12"Goodloe® packed column to afford 168 grams of product (b.p.: 100° C. at2 mmHg pressure).

FIG. 7 sets forth the GLC profile of the crude reaction product(conditions: 180° C., isothermal, 10'×1/4", 10% SE-30 packed column).

FIG. 8 sets forth the NMR spectrum for the reaction product consistingof 2-ethyl-5-(β-hydroxyethoxy)-tricyclo[2.2.1.0.sup.(2,6) ]heptane and2-ethylidene-6-(β-hydroxyethoxy)-norbornane having, respectively, thestructures: ##STR96##

FIG. 9 sets forth the infra red spectrum for the product mixtureconsisting of 2-ethyl-5-(β-hydroxyethyoxy)- tricyclo[2.2.1.0.sup.(2,6)]heptane and 2-ethylidene-6-(β-hydroxyethoxy) norbornane.

EXAMPLE IV PREPARATION OF A MIXTURE CONSISTING OF2-ETHYL-5-HEXYLOXYTRICYCLO[2.2.1.0.sup.(2,6) ]HEPTANE and2-ETHYLIDENE-6-HEXYLOXYNORBORNANE ##STR97##

Ethylidene norborene (480 grams) is added over a two hour period to astirred solution of hexyl alcohol (510 grams) and boron trifluorideetherate at 95° C. The reaction mass is poured into one liter of waterand the organic layer is subsequently washed with 500 mls of a 10%sodium carbonate solution. Distillation through a 11/2"×12" Goodloe®packed column affords 523 grams of product (b.p. 6° C. at 1 mmHgpressure).

FIG. 10 represents the GLC profile for the crude reaction product(conditions: 180° C., isothermal, 10'×1/4", 10% SE-30 packed column).

FIG. 11 sets forth the NMR spectrum of the product mixture consisting ofthe compounds having the structures: ##STR98##

FIG. 12 sets forth the infra red spectrum of the product mixtureconsisting of the compounds having the structures: ##STR99##

EXAMPLE V PREPARATION OF A MIXTURE CONSISTING OF 2-ETHYL-5-s-BUTYLOXYTRICYCLO[2.2.1.0.sup.(2,6) ]HEPTANE and2-ETHYLIDENE-6-s-BUTYLOXYNORBORNANE ##STR100##

Ethylidene norbornene (480 grams) is added over a two hour period to astirred solution of s-butyl alcohol (444 grams) and boron trifluorideetherate at 85° C. The reaction mass is poured into one liter of waterand the organic layer is washed with 500 ml of a 10% sodium carbonatesolution. Distillation through a 1'×11/2" Goodloe® packed column, afford513 grams of product (b.p. 78° C. at 5 mmHg pressure).

FIG. 13 sets forth the NMR spectrum of the product mixture consisting ofthe compounds have the structures: ##STR101##

FIG. 14 sets forth the infra red spectrum of the product mixtureconsisting of the compounds having the structures: ##STR102##

EXAMPLE VI PREPARATION OF A MIXTURE CONSISTING OF2-ETHYL-5-(β-METHOXYETHOXY)TRICYCLO[2.2.1.0.sup.(2,6) ]HEPTANE and2-ETHYLIDENE-6-(β-METHOXYETHOXY)NORBORNANE ##STR103##

Ethylidene norbornene (360 grams) is added to a stirred solution ofβ-methoxyethanol (304 grams) and boron trifluoride etherate (30 ml) at60° C. over a two hour period. The reaciton mass is then poured into 500ml of water and washed with a 10% sodium carbonate solution.Distillation through a 1"×12" Goodloe® packed column affords 348 gramsof product (b.p. 75° C. at 0.3 mmHg).

FIG. 15 sets forth GLC profile of the crude reaction product(conditions: 180° C., isothermal, 10'×1/4" 10%, SE-30 packed column).

FIG. 16 sets forth the NMR spectrum of the product mixture consisting ofthe compounds having the structures: ##STR104##

FIG. 17 sets forth the infra red spectrum of the product mixtureconsisting of the compounds having the structures: ##STR105##

EXAMPLE VII PREPARATION OF A MIXTURE CONSISTING OF2-ETHYL-5-ISOAMYLOXYTRICYCLO[2.2.1.0.sup.(2,6) ]HEPTANE and2-ETHYLIDENE-6-ISOAMYLOXYNORBORNANE ##STR106##

Ethylidene norbornene (408 grams) is added over a two hour period to asolution of isoamyl alchol (360 grams) and boron trifluoride etherate(30 ml) at 75° C. The reaction mixture is heated at 75° for a period oftwo hours whereupon it is quenched with one liter of water. The reactionmass is then washed with a 10% sodium carbonate solution. Distillationthrough a 11/2"×12" Goodloe® packed column affords 446 grams of product(b.p. 79° C. at 0.4 mmHg pressure).

FIG. 18 represents the GLC profile of the crude reaction product(conditions: 220° C., isothermal; 10'×1/4" 10%, SE-30 packed column).

FIG. 19 sets forth the NMR spectrum of the product mixture consisting ofthe compounds having the structures: ##STR107##

FIG. 20 sets forth the infra red spectrum of the product mixtureconsisting of the compounds having the structures: ##STR108##

EXAMPLE VIII PREPARATION OF A MIXTURE CONSISTING OF2-ETHYL-5-PHENETHYLOXYTRICYCLO[2.2.1.0.sup.(2,6) ]HEPTANE and2-ETHYLIDENE-6-PHENETHYLOXYNORBORNANE ##STR109##

Ethylidene norbornene (427 grams) is added over a two hour period to asolution of phenylethyl alcohol (379 grams) and boron trifluorideetherate (30 ml). The reaction mass is then heated to 100° C. for 90minutes. Water (one liter) is added and the reaction mass is washed witha 10% sodium carbonate solution. Distillation through a 11/2"×12"Goodloe® packed column affords 192 grams of product (b.p.: 105° C.-128°C. at 0.7 mmHg pressure).

FIG. 21 represents the GLC profile of the crude reaction product(conditions: 220° C., isothermal; 10'×1/4" 10%, SE-30 packed column).

FIG. 22 sets forth the NMR spectrum of the product mixture consisting ofthe compounds having the structures: ##STR110##

FIG. 23 sets forth the infra red spectrum of the product mixtureconsisting of the compounds having the structures: ##STR111##

EXAMPLE IX PREPARATION OF A MIXTURE CONSISTING OF2-ETHYL-5-(1',3'-DIMETHYLBUTYLOXY)TRICYCLO[2.2.1.0.sup.(2,6) ]HEPTANEand 2-ETHYLIDENE-6-(1',3'-DIMETHYLBUTYLOXY)NORBORNANE ##STR112##

Ethylidene norbornene (360 grams) is added to a solution of4-methyl-2-pentanol (408 grams) and boron trifluoride etherate (30 ml)over a two hour period at 60° C. The reaction mass is then heated at 75°C. for two hours and quenched in 500 ml of water. The resulting organiclayer is washed with 500 ml of a 10% sodium carbonate solution.Distillation through a 11/2"×12" Goodloe® packed column yields 236 gramsof product (b.p. 70° C. at 0.4 mmHg pressure).

FIG. 24 sets forth the GLC profile of the crude reaction mixture(conditions: 220° C., isothermal; 10'×1/4" 10%, SE-30 packed column).

FIG. 25 sets forth the NMR spectrum of the product consisting of thecompounds having the structures: ##STR113##

FIG. 26 sets forth the infra red spectrum of the reaction productconsisting of the compounds having the structures: ##STR114##

EXAMPLE X PREPARATION OF A MIXTURE CONSISTING OF2-ETHYL-5-ISOBUTYLOXYTRICYCLO[2.2.1.0.sup.(2,6) ]HEPTANE and2-ETHYLIDENE-6-ISOBUTYLOXYNORBORNANE ##STR115##

Ethylidene norbornene (480 grams) is added to a solution of isobutanol(407 grams) and boron trifluoride etherate at 80° C. over a 90 minuteperiod. The reaction mass is stirred at 80° C. for one hour whereupon700 ml of water is added thereto. The organic layer is washed with 500ml of a 10% sodium carbonate solution and distilled through a 1/2"×12"Goodloe® packed column to afford 662 grams of product (b.p. 55° C. at 1mmHg pressure).

FIG. 27 represents the GLC profile of the crude reaction product(conditions: 180° C.; isothermal, 10'×1/4" 10% SE-30 packed column).

FIG. 28 sets forth the NMR spectrum of the product mixture consisting ofthe compounds having the structures: ##STR116##

FIG. 29 sets forth the infra red spectrum of the reaction productmixture consisting of the compounds having the structures: ##STR117##EXAMPLE XI

PREPARATION OF A MIXTURE CONSISTING OF2-ETHYL-5-CYCLOHEXYLOXYTRICYCLO[2.2.1.0.sup.(2,6) ]HEPTANE and2-ETHYLIDENE-6-CYCLOHEXYLOXYNORBORNANE ##STR118##

Ethylidene norbornene (360 grams) is added to a stirred solution ofcyclohexanol (450 grams) and sulfuric acid (9 grams) at 80° C. over a 90minute period. The reaction mass is stirred at 90° C. for a further 90minutes whereupon 500 ml of water are added thereto. The organic layeris washed with 500 ml of a 10% sodium carbonate solution and distilledthrough a 11/2"×12" Goodloe® packed column to afford 528 grams ofproduct (b.p. 90° C. at 0.9 mmHg pressure).

FIG. 30 represents the GLC profile of the crude reaction product(conditions: 180° C., isothermal; 10'×1/4" SE-30 Packed column).

FIG. 31 represents the NMR spectrum of the reaction product mixtureconsisting of the compounds having the structures: ##STR119##

FIG. 32 sets forth the infra red spectrum of the reaction productmixture consisting of the compounds having the structures: ##STR120##

EXAMPLE XII

The following formulation is prepared:

    ______________________________________                                        Ingredients            Parts by Weight                                        ______________________________________                                        Turpentine gum oil     100                                                    Limonene               70                                                     Gum camphor            10                                                     Isobornyl acetate      50                                                     Borneol                30                                                     2-(2-Butenoyl)-3,3-dimethylnorbornane                                                                40                                                     (Produced according to Example XII                                            of U.S. Pat. No. 4,148,826)                                                   Mixture of 2-(3-butenoyl)-3,3-dimethyl-                                                              100                                                    norbornane and 2-(2-butenoyl)-3,3-                                            dimethylnorbornane (Produced according                                        to the process of Example III of U.S.                                         Pat. No. 4,148,826)                                                           Alpha-allyl-3,3-dimethyl-2-norbornane-                                                               70                                                     methanol (Produced according to the                                           process of Example II of U.S. Pat. No.                                        4,148,826)                                                                    ______________________________________                                    

EXAMPLE XII(A)

    __________________________________________________________________________                       Parts by Weight                                            Ingredient         "A"                                                                              "B"                                                                              "C"                                                                              "D"                                                                              "E"                                                                              "F"                                                                              "G"                                                                              "H"                                                                              "J"                                                                              "K"                                                                              "L"                          __________________________________________________________________________    The products produced according                                               to Example I, containing                                                      compounds having the structures:                                                                 60 0  0  0  0  0  0  0  0  0  0                             ##STR121##                                                                   and                                                                            ##STR122##                                                                   The product produced according                                                to Example II, containing                                                     compounds having the structures:                                                                 0  80 0  0  0  0  0  0  0  0  0                             ##STR123##                                                                   and                                                                            ##STR124##                                                                   The product produced according                                                to Example III, containing                                                    compounds having the structures:                                                                 0  0  90 0  0  0  0  0  0  0  0                             ##STR125##                                                                   and                                                                            ##STR126##                                                                   The product produced according                                                to Example IV containing the                                                  compounds having the structures:                                                                 0  0  0  90 0  0  0  0  0  0  0                             ##STR127##                                                                   and                                                                            ##STR128##                                                                   The product produced according                                                to Example V, containing the                                                  compounds having the structures:                                                                 0  0  0  0  80 0  0  0  0  0  0                             ##STR129##                                                                   and                                                                            ##STR130##                                                                   The product produced according to                                             Example VI, containing the                                                    compounds having the structures:                                                                 0  0  0  0  0  80 0  0  0  0  0                             ##STR131##                                                                   and                                                                            ##STR132##                                                                   The product produced according to                                             the process of Example VII, containing                                        the compounds having the structures:                                                             0  0  0  0  0  0  90 0  0  0  0                             ##STR133##                                                                   and                                                                            ##STR134##                                                                   The product produced according to the                                         process of Example VIII, containing                                           the compounds having the structures:                                                             0  0  0  0  0  0  0  80 0  0  0                             ##STR135##                                                                   and                                                                            ##STR136##                                                                   The product produced according to the                                         process of Example IX, containing                                             the compounds having the structures:                                                             0  0  0  0  0  0  0  0  70 0  0                             ##STR137##                                                                   and                                                                            ##STR138##                                                                   The product produced according to the                                         process of Example X, containing                                              the compounds having the structures:                                                             0  0  0  0  0  0  0  0  0  80 0                             ##STR139##                                                                   and                                                                            ##STR140##                                                                   The product produced according to the                                         process of Example XI, containing                                             the compounds having the structures:                                                             0  0  0  0  0  0  0  0  0  0  90                            ##STR141##                                                                   and                                                                            ##STR142##                                                                   __________________________________________________________________________

Each of Examples XII(A-L) has interesting pine needle oil aromas withvarious nuances described as follows:

                  TABLE II                                                        ______________________________________                                        Example      Aroma nuance                                                     ______________________________________                                        XII (A)      A fresh, green bean-like                                                      rosey, citrus, (petitgrain-                                                   like) aroma.                                                     XII (B)      A fruity, anisic, green aroma.                                   XII (C)      A green raw potato aroma with                                                 galbanum topnotes.                                               XII (D)      A long lasting, green, twiggy,                                                fruity and herbaceous aroma.                                     XII (E)      A sweet, fruity aroma.                                           XII (F)      An excellent green aroma.                                        XII (G)      A green, sweaty aroma.                                           XII (H)      A green pea-like and green                                                    aroma.                                                           XII (J)      A green and chocolate-like aroma                                              with anther-like undertones                                      XII (K)      A floral, green and carrot-like                                               aroma.                                                           XII (L)      A green, creamy, stringbean-                                                  like, herbaceous and floral-                                                  rosey aroma with anise-like                                                   undertones.                                                      ______________________________________                                    

EXAMPLE XIII PREPARATION OF A COSMETIC POWDER PREPARATION

A cosmetic powder is prepared by mixing in a ball mill, 100 g of talcumpowder with 0.25 g of one of the substances set forth in Table IIIbelow. The resulting cosmetic powder has a pleasant aroma as set forthin Table III below.

                  TABLE III                                                       ______________________________________                                        Structure of Compounds                                                                          Perfumery Evaluation                                        ______________________________________                                         ##STR143##       A fresh, green bean-like rosey, citrus, (petitgrain-                          like) aroma.                                                and                                                                            ##STR144##                                                                   Produced according to                                                         Example I                                                                      ##STR145##       A fruity, anisic, green aroma.                              and                                                                            ##STR146##                                                                   Produced according to                                                         Example II                                                                     ##STR147##       A green, raw potato aroma with galbanum topnotes.           and                                                                            ##STR148##                                                                   Produced according to                                                         Example III                                                                    ##STR149##       A long lasting, green, twiggy, fruity and herbaceous                          aroma.                                                      and                                                                            ##STR150##                                                                   Produced according to                                                         Example IV                                                                     ##STR151##       A sweet, fruity aroma.                                      and                                                                            ##STR152##                                                                   Produced according to                                                         Example V                                                                      ##STR153##       An excellent green aroma.                                   and                                                                            ##STR154##                                                                   Produced according to                                                         Example VI                                                                     ##STR155##       A green, sweaty aroma.                                      and                                                                            ##STR156##                                                                   Produced according to                                                         Example VII                                                                    ##STR157##       A green pea-like and green aroma.                           and                                                                            ##STR158##                                                                   Produced according to                                                         Example VIII                                                                   ##STR159##       A green and chocolate-like aroma with anther-like                             undertones.                                                  ##STR160##                                                                   Produced according to                                                         Example IX                                                                     ##STR161##       A floral, green and carrot-like aroma.                      and                                                                            ##STR162##                                                                   Produced according to                                                         Example X                                                                      ##STR163##       A green, creamy, string- bean-like, herbaceous and                            floral-rosey aroma with anise-like under- tones.            and                                                                            ##STR164##                                                                   Produced according to                                                         Example XI                                                                    ______________________________________                                        Each of Examples XII(A-L) has interesting pine needle                         oil aromas with various nuances described as follows:                         Example      Aroma nuance                                                     ______________________________________                                        XII(A)       A fresh, green bean-like                                                      rosey, citrus, (petitgrain-                                                   like) aroma.                                                     XII(B)       A fruity, anisic, green aroma.                                   XII(C)       A green raw potato aroma with                                                 galbanum topnotes.                                               XII(D)       A long lasting, green, twiggy,                                                fruity and herbaceous aroma.                                     XII(E)       A sweet, fruity aroma.                                           XII(F)       An excellent green aroma.                                        XII(G)       A green, sweaty aroma.                                           XII(H)       A green pea-like and green                                                    aroma.                                                           XII(J)       A green and chocolate-like aroma                                              with anther-like undertones.                                     XII(K)       A floral, green and carrot-like                                               aroma.                                                           XII(L)       A green, creamy, stringbean-                                                  like, herbaceous and floral-                                                  rosey aroma with anise-like                                                   undertones.                                                      ______________________________________                                    

EXAMPLE XIV

Concentrated liquid detergents (Lysine salt of n-dodecylbenzene sulfonicacid as more specifically described in U.S. Pat. No. 3,948,818, issuedon Apr. 6, 1976) with fragrance profiles as defined in Table IV beloware prepared containing 0.10%, 0.15%, 0.20%, 0.25%, 0.30% and 0.35% ofthe substance as set forth in Table IV below. They are prepared byadding and homogeneously mixing the appropriate quantity of substance asset forth in Table IV below in the liquid detergent. The detergents allpossess excellent intense aromas as defined according to the profiles ofTable IV below, the intensity increasing with greater concentrations ofsaid substance as set forth below in Table IV:

                  TABLE IV                                                        ______________________________________                                        Structure of Compounds                                                                          Perfumery Evaluation                                        ______________________________________                                         ##STR165##       A fresh, green bean-like rosey, citrus, (petitgrain-                          like) aroma.                                                and                                                                            ##STR166##                                                                   Produced according to                                                         Example I                                                                      ##STR167##       A fruity, anisic, green aroma.                              and                                                                            ##STR168##                                                                   Produced according to                                                         Example II                                                                     ##STR169##       A green, raw potato aroma with galbanum topnotes.           and                                                                            ##STR170##                                                                   Produced according to                                                         Example III                                                                    ##STR171##       A long lasting, green, twiggy, fruity and herbaceous                          aroma.                                                      and                                                                            ##STR172##                                                                   Produced according to                                                         Example IV                                                                     ##STR173##       A sweet, fruity aroma.                                      and                                                                            ##STR174##                                                                   Produced according to                                                         Example V                                                                      ##STR175##       An excellent green aroma.                                   and                                                                            ##STR176##                                                                   Produced according to                                                         Example VI                                                                     ##STR177##       A green, sweaty aroma.                                      and                                                                            ##STR178##                                                                   Produced according to                                                         Example VII                                                                    ##STR179##       A green pea-like and green aroma.                           and                                                                            ##STR180##                                                                   Produced according to                                                         Example VIII                                                                   ##STR181##       A green and chocolate-like aroma with anther-like                             undertones.                                                  ##STR182##                                                                   Produced according to                                                         Example IX                                                                     ##STR183##       A floral, green and carrot-like aroma.                      and                                                                            ##STR184##                                                                   Produced according to                                                         Example X                                                                      ##STR185##       A green, creamy, string- bean-like, herbaceous and                            floral-rosey aroma with anise-like under- tones.            and                                                                            ##STR186##                                                                   Produced according to                                                         Example XI                                                                    ______________________________________                                        Each of Examples XII(A-L) has interesting pine needle                         oil aromas with various nuances described as follows:                         Example      Aroma nuance                                                     ______________________________________                                        XII(A)       A fresh, green bean-like                                                      rosey, citrus, (petitgrain-                                                   like) aroma.                                                     XII(B)       A fruity, anisic, green aroma.                                   XII(C)       A green raw potato aroma with                                                 galbanum topnotes.                                               XII(D)       A long lasting, green, twiggy,                                                fruity and herbaceous aroma.                                     XII(E)       A sweet, fruity aroma.                                           XII(F)       An excellent green aroma.                                        XII(G)       A green, sweaty aroma.                                           XII(H)       A green pea-like and green                                                    aroma.                                                           XII(J)       A green and chocolate-like aroma                                              with anther-like undertones.                                     XII(K)       A floral, green and carrot-like                                               aroma.                                                           XII(L)       A green, creamy, stringbean-                                                  like, herbaceous and floral-                                                  rosey aroma with anise-like                                                   undertones.                                                      ______________________________________                                    

EXAMPLE XV PREPARATION OF A COLOGNE AND HANDKERCHIEF PERFUME

Substances set forth in Table V below are each individually incorporatedinto colognes at concentrations of 2.0%, 2.5%, 3.0%, 3.5%, 4.0%, 4.5%and 5.0% in (75%, 80%, 85% and 90%, aqueous food grade ethanol); andinto handkerchief perfumes at concentrations of 15%, 20%, 25% and 30%(in 95% aqueous food grade ethanol). Distinctive and definitivelong-lasting warm aromas as defined according to Table V below are allimparted to the cologne and to the handkerchief perfumes at all levelsas indicated above:

                  TABLE V                                                         ______________________________________                                        Structure of Compounds                                                                          Perfumery Evaluation                                        ______________________________________                                         ##STR187##       A fresh, green bean-like rosey, citrus, (petitgrain-                          like) aroma.                                                and                                                                            ##STR188##                                                                   Produced according to                                                         Example I                                                                      ##STR189##       A fruity, anisic, green aroma.                              and                                                                            ##STR190##                                                                   Produced according to                                                         Example II                                                                     ##STR191##       A green, raw potato aroma with galbanum topnotes.           and                                                                            ##STR192##                                                                   Produced according to                                                         Example III                                                                    ##STR193##       A long lasting, green, twiggy, fruity and herbaceous                          aroma.                                                      and                                                                            ##STR194##                                                                   Produced according to                                                         Example IV                                                                     ##STR195##       A sweet, fruity aroma.                                      and                                                                            ##STR196##                                                                   Produced according to                                                         Example V                                                                      ##STR197##       An excellent green aroma.                                   and                                                                            ##STR198##                                                                   Produced according to                                                         Example VI                                                                     ##STR199##       A green, sweaty aroma.                                      and                                                                            ##STR200##                                                                   Produced according to                                                         Example VII                                                                    ##STR201##       A green pea-like and green aroma.                           and                                                                            ##STR202##                                                                   Produced according to                                                         Example VIII                                                                   ##STR203##       A green and chocolate-like aroma with anther-like                             undertones.                                                  ##STR204##                                                                   Produced according to                                                         Example IX                                                                     ##STR205##       A floral, green and carrot-like aroma.                      and                                                                            ##STR206##                                                                   Produced according to                                                         Example X                                                                      ##STR207##       A green, creamy, string- bean-like, herbaceous and                            floral-rosey aroma with anise-like under- tones.            and                                                                            ##STR208##                                                                   Produced according to                                                         Example XI                                                                    ______________________________________                                        Each of Examples XII(A-L) has interesting pine needle                         oil aromas with various nuances described as follows:                         Example      Aroma nuance                                                     ______________________________________                                        XII(A)       A fresh, green bean-like                                                      rosey, citrus, (petitgrain-                                                   like) aroma.                                                     XII(B)       A fruity, anisic, green aroma.                                   XII(C)       A green raw potato aroma with                                                 galbanum topnotes.                                               XII(D)       A long lasting, green, twiggy,                                                fruity and herbaceous aroma.                                     XII(E)       A sweet, fruity aroma.                                           XII(F)       An excellent green aroma.                                        XII(G)       A green, sweaty aroma.                                           XII(H)       A green pea-like and green                                                    aroma.                                                           XII(J)       A green and chocolate-like aroma                                              with anther-like undertones.                                     XII(K)       A floral, green and carrot-like                                               aroma.                                                           XII(L)       A green, creamy, stringbean-                                                  like, herbaceous and floral-                                                  rosey aroma with anise-like                                                   undertones.                                                      ______________________________________                                    

EXAMPLE XVI PREPARATION OF SOAP COMPOSITION

One hundred grams of soap chips (IVORY®, produced by the Proctor &Gamble Company, Cinncinati, Ohio) are admixed with one gram of thesubstance as set forth in Table VI below until homogeneous compositionsare obtained. In each of the cases, the homogeneous compositions areheated under three atmospheres pressure at 180° C. for a period of threehours and the resulting liquids are placed into soap molds. Theresulting soap cakes, on cooling, manifest excellent, long-lasting, warmaromas as set forth in the Table VI below:

                  TABLE VI                                                        ______________________________________                                        Structure of Compounds                                                                          Perfumery Evaluation                                        ______________________________________                                         ##STR209##       A fresh, green bean-like rosey, citrus, (petitgrain-                          like) aroma.                                                and                                                                            ##STR210##                                                                   Produced according to                                                         Example I                                                                      ##STR211##       A fruity, anisic, green aroma.                              and                                                                            ##STR212##                                                                   Produced according to                                                         Example II                                                                     ##STR213##       A green, raw potato aroma with galbanum topnotes.           and                                                                            ##STR214##                                                                   Produced according to                                                         Example III                                                                    ##STR215##        A long lasting, green, twiggy, fruity and herbaceous                         aroma.                                                      and                                                                            ##STR216##                                                                   Produced according to                                                         Example IV                                                                     ##STR217##       A sweet, fruity aroma.                                      and                                                                            ##STR218##                                                                   Produced according to                                                         Example V                                                                      ##STR219##       An excellent green aroma.                                   and                                                                            ##STR220##                                                                   Produced according to                                                         Example VI                                                                     ##STR221##       A green, sweaty aroma.                                      and                                                                            ##STR222##                                                                   Produced according to                                                         Example VII                                                                    ##STR223##       A green pea-like and green aroma.                           and                                                                            ##STR224##                                                                   Produced according to                                                         Example VIII                                                                   ##STR225##       A green and chocolate-like aroma with anther-like                             undertones                                                   ##STR226##                                                                   Produced according to                                                         Example IX                                                                     ##STR227##       A floral, green and carrot-like aroma.                      and                                                                            ##STR228##                                                                   Produced according to                                                         Example X                                                                      ##STR229##       A green, creamy, string-  bean-like, herbaceous and                           floral-rosey aroma with anise-like under- tones.            and                                                                            ##STR230##                                                                   Produced according to                                                         Example XI                                                                    ______________________________________                                        Each of Example XII(A-L) has interesting pine needle                          oil aromas with various nuances described as follows:                         Example      Aroma nuance                                                     ______________________________________                                        XII(A)       A fresh, green bean-like                                                      rosey, citrus, (petitgrain-                                                   like) aroma.                                                     XII(B)       A fruity, anisic, green aroma.                                   XII(C)       A green raw potato aroma with                                                 galbanum topnotes.                                               XII(D)       A long lasing, green, twiggy,                                                 fruity and herbaceous aroma.                                     XII(E)       A sweet, fruity aroma.                                           XII(F)       An excellent green aroma.                                        XII(G)       A green, sweaty aroma.                                           XII(H)       A green pea-like and green                                                    aroma.                                                           XII(J)       A green and chocolate-like aroma                                              with anther-like undertones                                      XII(K)       A floral, green and carrot-like                                               aroma.                                                           XII(L)       A green, creamy, stringbean-                                                  like, herbaceous and floral-                                                  rosey aroma with anise-like                                                   undertones.                                                      ______________________________________                                    

EXAMPLE XVII PREPARATION OF SOLID DETERGENT COMPOSITIONS

Detergents are prepared from the following ingredients according toExample I of Canadian Pat. No. 1,007,948:

    ______________________________________                                        Ingredient        Percent by Weight                                           ______________________________________                                        Neodol® 45-11 (a C.sub.14 -C.sub.15                                                         12                                                          Alcohol ethoxylated with                                                      11 moles of ethylene oxide)                                                   Sodium carbonate  55                                                          Sodium citrate    20                                                          Sodium sulfate, water                                                                           q.s.                                                        brighteners                                                                   ______________________________________                                    

This detergent is a "phosphate-free" detergent. A total of 100 grams ofsaid detergent is admixed with 0.10, 0.15, 0.20 and 0.25 grams of thesubstance as set forth in Table VII below. Each of the detergent sampleshave excellent, warm aromas as indicated in Table VII below:

                  TABLE VII                                                       ______________________________________                                        Structure of Compounds                                                                          Perfumery Evaluation                                        ______________________________________                                         ##STR231##       A fresh, green bean-like rosey, citrus, (petitgrain-                          like) aroma.                                                and                                                                            ##STR232##                                                                   Produced according to                                                         Example I                                                                      ##STR233##       A fruity, anisic, green aroma.                              and                                                                            ##STR234##                                                                   Produced according to                                                         Example II                                                                     ##STR235##       A green, raw potato aroma with galbanum topnotes.           and                                                                            ##STR236##                                                                   Produced according to                                                         Example III                                                                    ##STR237##       A long lasting, green, twiggy, fruity and herbaceous                          aroma.                                                      and                                                                            ##STR238##                                                                   Produced according to                                                         Example IV                                                                     ##STR239##       A sweet, fruity aroma.                                      and                                                                            ##STR240##                                                                   Produced according to                                                         Example V                                                                      ##STR241##       An excellent green aroma.                                   and                                                                            ##STR242##                                                                   Produced according to                                                         Example VI                                                                     ##STR243##       A green, sweaty aroma.                                      and                                                                            ##STR244##                                                                   Produced according to                                                         Example VII                                                                    ##STR245##       A green pea-like and green aroma.                           and                                                                            ##STR246##                                                                   Produced according to                                                         Example VIII                                                                   ##STR247##       A green and chocolate-like aroma with anther-like                             undertones                                                   ##STR248##                                                                   Produced according to                                                         Example IX                                                                     ##STR249##       A floral, green and carrot-like aroma.                      and                                                                            ##STR250##                                                                   Produced according to                                                         Example X                                                                      ##STR251##       A green, creamy, string-  bean-like, herbaceous and                           floral-rosey aroma with anise-like under- tones.            and                                                                            ##STR252##                                                                   Produced according to                                                         Example XI                                                                    ______________________________________                                        Each of Examples XII(A-L) has interesting pine needle                         oil aromas with various nuances described as follows:                         Example      Aroma nuance                                                     ______________________________________                                        XII(A)       A fresh, green bean-like                                                      rosey, citrus, (petitgrain-                                                   like) aroma.                                                     XII(B)       A fruity, anisic, green aroma.                                   XII(C)       A green raw potato aroma with                                                 galbanum topnotes.                                               XII(D)       A long lasting, green, twiggy,                                                fruity and herbaceous aroma.                                     XII(E)       A sweet, fruity aroma.                                           XII(F)       An excellent green aroma.                                        XII(G)       A green, sweaty aroma.                                           XII(H)       A green pea-like and green                                                    aroma.                                                           XII(J)       A green and chocolate-like aroma                                              with anther-like undertones                                      XII(K)       A floral, green and carrot-like                                               aroma.                                                           XII(L)       A green, creamy, stringbean-                                                  like, herbaceous and floral-                                                  rosey aroma with anise-like                                                   undertones.                                                      ______________________________________                                    

EXAMPLE XVIII

Utilizing the procedure of Example I of column 15 of U.S. Pat. No.3,632,396, a non-woven cloth substrate useful as a dryer-added fabricsoftening article of manufacture prepared wherein the substrate, thesubstrate coating and the outer coating and the perfuming material areas follows:

1. A water "dissolvable" paper ("Dissolvo Paper")

2. Adogen 448 (m.p. about 140° F.) as the substrate coating; and

3. An outer coating having the following formulation (m.p. about 150°F.):

57 percent C₂₀ -C₂₂ HAPS

22 percent isopropyl alcohol

20 percent antistatic agent

1 percent of one of the substances as set forth in Table VIII below.

Fabric softening compositions containing substances as set forth inTable VIII below essentially consist of a substrate having a weight ofabout 3 grams per 100 square inches of substrate coating, of about 1.85grams per 100 square inches of substrate, and an outer coating of about1.4 grams per 100 square inches of substrate, thereby providing a totalamoratized substrate and outer coating weight ration of about 1:1 byweight of the substrate. The aromas as set forth in Table VIII below,are imparted in a pleasant manner, to the head space in the dryer onoperation thereof, using the said dryer-added fabric softening non-wovenfabric:

                  TABLE VIII                                                      ______________________________________                                        Structure of Compounds                                                                          Perfumery Evaluation                                        ______________________________________                                         ##STR253##       A fresh, green bean-like rosey, citrus, (petitgrain-                          like) aroma.                                                and                                                                            ##STR254##                                                                   Produced according to                                                         Example I                                                                      ##STR255##                                                                   and                                                                            ##STR256##                                                                   Produced according to                                                         Example II                                                                     ##STR257##       A green, raw potato aroma with galbanum topnotes.           and                                                                            ##STR258##                                                                   Produced according to                                                         Example III                                                                    ##STR259##       A long lasting, green, twiggy, fruity and  herbaceous                         aroma.                                                      and                                                                            ##STR260##                                                                   Produced according to                                                         Example IV                                                                     ##STR261##       A sweet, fruity aroma.                                      and                                                                            ##STR262##                                                                   Produced according to                                                         Example V                                                                      ##STR263##       An excellent green aroma.                                   and                                                                            ##STR264##                                                                   Produced according to                                                         Example VI                                                                     ##STR265##       A green, sweaty aroma.                                      and                                                                            ##STR266##                                                                   Produced according to                                                         Example VII                                                                    ##STR267##       A green pea-like and green aroma.                           and                                                                            ##STR268##                                                                   Produced according to                                                         Example VIII                                                                   ##STR269##       A green and chocolate-like aroma with anther-like                             undertones                                                   ##STR270##                                                                   Produced according to                                                         Example IX                                                                     ##STR271##       A floral, green and carrot-like aroma.                      and                                                                            ##STR272##                                                                   Produced according to                                                         Example X                                                                      ##STR273##       A green, creamy, string-  bean-like, herbaceous and                           floral-rosey aroma with anise-like under- tones.            and                                                                            ##STR274##                                                                   Produced according to                                                         Example XI                                                                    ______________________________________                                        Each of Examples XII(A-L) has interesting pine needle                         oil aromas with various nuances described as follows:                         Example      Aroma nuance                                                     ______________________________________                                        XII(A)       A fresh, green bean-like                                                      rosey, citrus, (petitgrain-                                                   like) aroma.                                                     XII(B)       A fruity, anisic, green aroma.                                   XII(C)       A green raw potato aroma with                                                 galbanum topnotes.                                               XII(D)       A long lasting, green, twiggy,                                                fruity and herbaceous aroma.                                     XII(E)       A sweet, fruity aroma.                                           XII(F)       An excellent green aroma.                                        XII(G)       A green, sweaty aroma.                                           XII(H)       A green pea-like and green                                                    aroma.                                                           XII(J)       A green and chocolate-like aroma                                              with anther-like undertones                                      XII(K)       A floral, green and carrot-like                                               aroma.                                                           XII(L)       A green, creamy, stringbean-                                                  like, herbaceous and floral-                                                  rosey aroma with anise-like                                                   undertones.                                                      ______________________________________                                    

In the following examples, Aromox® DMC-W and Aromox® DMMC-W are 30%aqueous solutions of dimethyl cocoamine oxide; and Aromox® NCMDW is a40% aqueous solution of N-cocomorpholine oxide produced by Armacdivision of AKZO of Chicago, Ill.

EXAMPLE XIX

Four drops of one of the substances set forth in Table IX below is addedto two grams of Aromox® DMC-W to produce a clear premix. The clearpremix is added to 200 grams of CLOROX® with stirring resulting in aclear stable, single phase solution. Sufficient 1 M aqueous NaOH isadded to bring the pH of the mixture up to 12.8. The solution remainssubstantially stable at 120° F. for a period of seven days. When the 5%aqueous sodium hypochlorite solution is used as a laundry bleach, theresulting laundry, on dry-out in an atmosphere of 65% relative humidityyields substantially no characteristic "hypochlorite" odor, but doeshave a faint pleasant aroma as set forth in Table IX below. Furthermore,no such characteristic "hyprochlorite" aroma is retained on the hands ofthe individual handling such laundry in both the wet and the dry states:

                  TABLE IX                                                        ______________________________________                                        Structure of Compounds                                                                          Perfumery Evaluation                                        ______________________________________                                         ##STR275##       A fresh, green bean-like rosey, citrus, (petitgrain-                          like) aroma.                                                and                                                                            ##STR276##                                                                   Produced according to                                                         Example I                                                                      ##STR277##       A fruity, anisic, green aroma.                              and                                                                            ##STR278##                                                                   Produced according to                                                         Example II                                                                     ##STR279##       A green, raw potato aroma with galbanum topnotes.           and                                                                            ##STR280##                                                                   Produced according to                                                         Example III                                                                    ##STR281##       A long lasting, green, twiggy, fruity and herbaceous                          aroma.                                                      and                                                                            ##STR282##                                                                   Produced according to                                                         Example IV                                                                     ##STR283##       A sweet, fruity aroma.                                      and                                                                            ##STR284##                                                                   Produced according to                                                         Example V                                                                      ##STR285##       An excellent green aroma.                                   and                                                                            ##STR286##                                                                   Produced according to                                                         Example VI                                                                     ##STR287##       A green, sweaty aroma.                                      and                                                                            ##STR288##                                                                   Produced according to                                                         Example VII                                                                    ##STR289##       A green pea-like and green aroma.                           and                                                                            ##STR290##                                                                   Produced according to                                                         Example VIII                                                                   ##STR291##       A green and chocolate-like aroma with anther-like                             undertones                                                   ##STR292##                                                                   Produced according to                                                         Example IX                                                                     ##STR293##       A floral, green and carrot-like aroma.                      and                                                                            ##STR294##                                                                   Produced according to                                                         Example X                                                                      ##STR295##        A green, creamy, string- bean-like, herbaceous and                           floral-rosey aroma with anise-like under- tones.            and                                                                            ##STR296##                                                                   Produced according to                                                         Example XI                                                                    ______________________________________                                        Each of Examples XII(A-L) has interesting pine needle                         oil aromas with various nuances described as follows:                         Example      Aroma nuance                                                     ______________________________________                                        XII(A)       A fresh, green bean-like                                                      like) aroma.                                                     XII(B)       A fruity, anisic, green aroma.                                   XII(C)       A green raw potato aroma with                                                 galbanum topnotes.                                               XII(D)       A long lasting, green, twiggy,                                                fruity and herbaceous aroma.                                     XII(E)       A sweet, fruity aroma.                                           XII(F)       An excellent green aroma.                                        XII(G)       A green, sweaty aroma.                                           XII(H)       A green pea-like and green                                                    aroma.                                                           XII(J)       A green and chocolate-like aroma                                              with anther-like undertones                                      XII(K)       A floral, green and carrot-like                                               aroma.                                                           XII(L)       A green, creamy, stringbean-                                                  like, herbaceous and floral-                                                  rosey aroma with anise-like                                                   undertones.                                                      ______________________________________                                    

EXAMPLE XX

Amorox® DMMC-W in various quantities is mixed with 0.1 grams of one ofthe substances set forth in Table X below. The resulting premixes arethen added to 200 grams of an aqueous 5% sodium hypochlorite solution.Sufficient 12.5 M aqueous NaOH is added to bring the pH of the mixtureup to 13. The following results are obtained:

    ______________________________________                                        Percentage Aromox®                                                                         Clarity of hypochlorite solu-                                DMMC-W           tion after addition of premix                                ______________________________________                                        0.23%            Clear after three days                                       0.15%            Clear after three days                                       0.08%            Initially slightly turbid;                                                    two phases exist after                                                        three days.                                                  ______________________________________                                    

When the 5% aqueous sodium hypochlorite solution is used as a laundrybleach, the resulting laundry on dry-out, in an atmosphere of 65%relative humidity, yields substantially no characteristic "hypochlorite"odor, but does have a faint, pleaseant aroma as set forth in Table Xbelow. Furthermore, no such characteristic "hypochlorite" aroma isretained on the hands of the individual handling such laundry in boththe wet and the dry states:

                  TABLE X                                                         ______________________________________                                        Structure of Compounds                                                                          Perfumery Evaluation                                        ______________________________________                                         ##STR297##       A fresh, green bean-like rosey, citrus, (petitgrain-                          like) aroma.                                                 ##STR298##                                                                   Produced according to                                                         Example I                                                                      ##STR299##       A fruity, anisic, green aroma.                              and                                                                            ##STR300##                                                                   Produced according to                                                         Example II                                                                     ##STR301##       A green, raw potato aroma with galbanum topnotes.           and                                                                            ##STR302##                                                                   Produced according to                                                         Example III                                                                    ##STR303##       A long lasting, green, twiggy, fruity and herbaceous                          aroma.                                                      and                                                                            ##STR304##                                                                   Produced according to                                                         Example IV                                                                     ##STR305##       A sweet, fruity aroma.                                      and                                                                            ##STR306##                                                                   Produced according to                                                         Example V                                                                      ##STR307##       An excellent green aroma.                                   and                                                                            ##STR308##                                                                   Produced according to                                                         Example VI                                                                     ##STR309##       A green, sweaty aroma.                                      and                                                                            ##STR310##                                                                   Produced according to                                                         Example VII                                                                    ##STR311##       A green pea-like and green aroma.                           and                                                                            ##STR312##                                                                   and                                                                           Produced according to                                                         Example VIII                                                                   ##STR313##       A green and chocolate-like aroma with anther-like                             undertones                                                   ##STR314##                                                                   Produced according to                                                         Example IX                                                                     ##STR315##       A floral, green and carrot-like aroma.                      and                                                                            ##STR316##                                                                   Produced according to                                                         Example X                                                                      ##STR317##       A green, creamy, string- bean-like, herbaceous and                            floral-rosey aroma with anise-like under- tones.            and                                                                            ##STR318##                                                                   Produced according to                                                         Example XI                                                                    ______________________________________                                        Each of Examples XII(A-L) has interesting pine needle                         oil aromas with various nuances described as follows:                         Example      Aroma nuance                                                     ______________________________________                                        XII(A)       A fresh, green bean-like                                                      rosey, citrus, (petitgrain-                                                   like) aroma.                                                     XII(B)       A fruity, anisic, green aroma.                                   XII(C)       A green raw potato aroma with                                                 galbanum topnotes.                                               XII(D)       A long lasting, green, twiggy,                                                fruity and herbaceous aroma.                                     XII(E)       A sweet, fruity aroma.                                           XII(F)       An excellent green aroma.                                        XII(G)       A green, sweaty aroma.                                           XII(H)       A green pea-like and green                                                    aroma.                                                           XII(J)       A green and chocolate-like aroma                                              with anther-like undertones                                      XII(K)       A floral, green and carrot-like                                               aroma.                                                           XII(L)       A green, creamy, stringbean-                                                  like, herbaceous and floral-                                                  rosey aroma with anise-like                                                   undertones.                                                      ______________________________________                                    

EXAMPLE XXI

Two grams of Aromox® DMMC-W is admixed with eight drops of one of thesubstances set forth in Table XI below. The premix is then added withstirring to 200 grams of a 7% aqueous solution of lithium hypochlorite.Sufficient 3 M aqueous LiOH is added to bring the pH of the solution to13.4. The mixture is then heated to 120° F. and maintained at thattemperature with stirring for a period of 1 week. The resulting solutionremains clear in a single phase. When used as a laundry bleach, theresulting bleached laundry, on dry-out in an atmosphere of 50% relativehumidity retains a "clean" warm aroma as set forth in Table XI below;whereas without the use of the substance set forth in Table XI below,the bleached laundry has a faint characteristic disagreeable"hypochlorite" aroma.

                  TABLE XI                                                        ______________________________________                                        Structure of Compounds                                                                          Perfumery Evaluation                                        ______________________________________                                         ##STR319##       A fresh, green bean-like rosey, citrus, (petitgrain-                          like) aroma.                                                and                                                                            ##STR320##                                                                   Produced according to                                                         Example I                                                                      ##STR321##       A fruity, anisic, green aroma.                              and                                                                            ##STR322##                                                                   Produced according to                                                         Example II                                                                     ##STR323##       A green, raw potato aroma with galbanum topnotes.           and                                                                            ##STR324##                                                                   Produced according to                                                         Example III                                                                    ##STR325##       A long lasting, green, twiggy, fruity and herbaceous                          aroma.                                                      and                                                                            ##STR326##                                                                   Produced according to                                                         Example IV                                                                     ##STR327##       A sweet, fruity aroma.                                      and                                                                            ##STR328##                                                                   Produced according to                                                         Example V                                                                      ##STR329##       An excellent green aroma.                                   and                                                                            ##STR330##                                                                   Produced according to                                                         Example VI                                                                     ##STR331##       A green, sweaty aroma.                                      and                                                                            ##STR332##                                                                   Produced according to                                                         Example VII                                                                    ##STR333##       A green pea-like and green aroma.                           and                                                                            ##STR334##                                                                   Produced according to                                                         Example VIII                                                                   ##STR335##       A green and chocolate-like aroma with anther-like                             undertones                                                   ##STR336##                                                                   Produced according to                                                         Example IX                                                                     ##STR337##       A floral, green and carrot-like aroma.                      and                                                                            ##STR338##                                                                   Produced according to                                                         Example X                                                                      ##STR339##       A green, creamy, string- bean-like, herbaceous and                            floral-rosey aroma with anise-like under- tones.            and                                                                            ##STR340##                                                                   Produced according to                                                         Example XI                                                                    ______________________________________                                        Each of Examples XII(A-L) has interesting pine needle                         oil aromas with various nuances described as follows:                         Example      Aroma nuance                                                     ______________________________________                                        XII(A)       A fresh, green bean-like                                                      rosey, citrus, (petitgrain-                                                   like) aroma.                                                     XII(B)       A fruity, anisic, green aroma.                                   XII(C)       A green raw potato aroma with                                                 galbanum topnotes.                                               XII(D)       A long lasting, green twiggy,                                                 fruity and herbaceous aroma.                                     XII(E)       A sweet, fruity aroma.                                           XII(F)       An excellent green aroma.                                        XII(G)       A green sweaty aroma.                                            XII(H)       A green pea-like and green                                                    aroma.                                                           XII(J)       A green and chocolate-like aroma                                              with anther-like undertones.                                     XII(K)       A floral, green and carrot-like                                               aroma.                                                           XII(L)       A green, creamy, stringbean-                                                  like, herbaceous and floral-                                                  rosey aroma with anise-like                                                   undertones.                                                      ______________________________________                                    

EXAMPLE XXII

Two grams of Aromox® DMMC-W is admixed with eight drops of one of thesubstance of Table XII below. This premix is then added, with stirringto 200 grams of a mixture containing 4.5% aqueous sodium hypochloriteand 4.5% aqueous lithium hypochlorite. Sufficient 4 M aqueous LiOH isadded to bring the pH of the solution to 13.4. The mixture is thenheated to 120° F. and maintained at that temperature for a period of oneweek. The resulting solution remains clear in a single phase. When usedas a laundry bleach, the resulting bleached laundry on dry-out in anatmosphere of 50% relative humidity retains a "clean fresh" warm aromaas set forth in Table VII below; whereas without the use of thesubstance set forth in Table VII below, the bleached laundry has a faintcharacteristic disagreeable "hypochlorite" aroma:

                  TABLE XII                                                       ______________________________________                                        Structure of Compounds                                                                          Perfumery Evaluation                                        ______________________________________                                         ##STR341##       A fresh, green bean-like rosey, citrus                                        (petit- grain-like) aroma.                                  and                                                                            ##STR342##                                                                   Produced according to                                                         Example I                                                                      ##STR343##       A long lasting, green, twiggy, fruity and herbaceous                          aroma.                                                      and                                                                            ##STR344##                                                                   Produced according to                                                         Example IV                                                                     ##STR345##       A sweet, fruity aroma.                                      and                                                                            ##STR346##                                                                   Produced according to                                                         Example V                                                                      ##STR347##        A long lasting, green, twiggy, fruity and herbaceous                         aroma.                                                      and                                                                            ##STR348##                                                                   Produced according to                                                         Example IV                                                                     ##STR349##       A sweet, fruity aroma.                                      and                                                                            ##STR350##                                                                   Produced according to                                                         Example V                                                                      ##STR351##       An excellent green aroma.                                   and                                                                            ##STR352##                                                                   Produced according to                                                         Example VI                                                                     ##STR353##       A green, sweaty aroma.                                      and                                                                            ##STR354##                                                                   Produced according to                                                         Example VII                                                                    ##STR355##       A green pea-like and green aroma.                           and                                                                            ##STR356##                                                                   Produced according to                                                         Example VIII                                                                   ##STR357##       A green and chocolate-like aroma with anther-like                             undertones                                                   ##STR358##                                                                   Produced according to                                                         Example IX                                                                     ##STR359##       A floral, green and carrot-like aroma.                      and                                                                            ##STR360##                                                                   Produced according to                                                         Example X                                                                      ##STR361##       A green, creamy, string- bean-like, herbaceous and                            floral-rosey aroma with anise-like under- tones.            and                                                                            ##STR362##                                                                   Produced according to                                                         Example XI                                                                    ______________________________________                                        Each of Example XII(A-L) has interesting pine needle                          oil aromas with various nuances described as follows:                         Example      Aroma nuance                                                     ______________________________________                                        XII(A)       A fresh, green bean-like                                                      rosey, citrus, (petitgrain-                                                   like aroma.                                                      XII(B)       A fruity, anisic, green aroma.                                   XII(C)       A green raw potato aroma with                                                 galbanum topnotes.                                               XII(D)       A long lasting, green, twiggy,                                                fruity and herbaceous aroma.                                     XII(E)       A sweet, fruity aroma.                                           XII(F)       An excellent green aroma.                                        XII(G)       A green, sweaty aroma.                                           XII(H)       A green pea-like and green                                                    aroma.                                                           XII(J)       A green and chocolate-like aroma                                              with anther-like undertones                                      XII(K)       A floral, green and carrot-like                                               aroma.                                                           XII(L)       A green, creamy, stringbean-                                                  like, herbaceous and floral-                                                  rosey aroma with anise-like                                                   undertones.                                                      ______________________________________                                    

EXAMPLE XXIII

Two grams of Aromox® DMMC-W is admixed with eight drops of one of thesubstances set forth in Table XIII below. This premix is then added withstirring to 200 grams of a mixture containing 4.5% aqueous sodiumhypochlorite and 4.5% aqueous lithium hypochlorite. Sufficient 2 Maqueous NaOH is added to bring the pH of the solution to 13.4. Themixture is then heated to 110° F. and maintained at that temperaturewith stirring for a period of 2 weeks. The resulting solution remainsclear as a single phase when used as a laundry bleach. The resultinglaundry bleach, on dry-out in an atmosphere of 50% relative humidity,retains an aroma as set forth in Table XIII below, whereas without theuse of the substance set forth in Table XIII below, the bleached laundryhas a faint characteristic disagreeable "hypochlorite" aroma.

                  TABLE XIII                                                      ______________________________________                                        Structure of Compound                                                                           Perfumery Evaluation                                        ______________________________________                                         ##STR363##       A fresh, green bean-like rosey, citrus, (petitgrain-                          like) aroma.                                                 ##STR364##                                                                   Produced according to                                                         Example I                                                                      ##STR365##       A fruity, anisic, green aroma.                              and                                                                            ##STR366##                                                                   Produced according to                                                         Example II                                                                     ##STR367##       A green, raw potato aroma with galbanum topnotes.           and                                                                            ##STR368##                                                                   Produced according to                                                         Example III                                                                    ##STR369##       A long lasting, green, twiggy, fruity and herbaceous                          aroma.                                                      and                                                                            ##STR370##                                                                   Produced according to                                                         Example IV                                                                     ##STR371##       A sweet, fruity aroma.                                      and                                                                            ##STR372##                                                                   Produced according to                                                         Example V                                                                      ##STR373##       An excellent green aroma.                                   and                                                                            ##STR374##                                                                   Produced according to                                                         Example VI                                                                     ##STR375##       A green, sweaty aroma.                                      and                                                                            ##STR376##                                                                   Produced according to                                                         Example VII                                                                    ##STR377##       A green pea-like and green aroma.                           and                                                                            ##STR378##                                                                   and                                                                           Produced according to                                                         Example VIII                                                                   ##STR379##       A green and chocolate-like aroma with anther-like                             undertones                                                   ##STR380##                                                                   Produced according to                                                         Example IX                                                                     ##STR381##       A floral, green and carrot-like aroma.                      and                                                                            ##STR382##                                                                   Produced according to                                                         Example X                                                                      ##STR383##       A green, creamy, string- bean-like, herbaceous and                            floral-rosey aroma with anise-like under- tones.            and                                                                            ##STR384##                                                                   Produced according to                                                         Example XI                                                                    ______________________________________                                        Each of Examples XII(A-L) has interesting pine needle                         oil aromas with various nuances described as follows:                         Example      Aroma nuance                                                     ______________________________________                                        XII(A)       A fresh, green bean-like                                                      rosey, citrus, (petitgrain-                                                   like) aroma.                                                     XII(B)       A fruity, anisic, green aroma.                                   XII(C)       A green raw potato aroma with                                                 galbanum topnotes.                                               XII(D)       A long lasting, green, twiggy,                                                fruity and herbaceous aroma.                                     XII(E)       A sweet, fruity aroma.                                           XII(F)       An excellent green aroma.                                        XII(G)       A green, sweaty aroma.                                           XII(H)       A green pea-like and green                                                    aroma.                                                           XII(J)       A green and chocolate-like aroma                                              with anther-like undertones                                      XII(K)       A floral, green and carrot-like                                               aroma.                                                           XII(L)       A green, creamy, stringbean-                                                  like, herbaceous and floral-                                                  rosey aroma with anise-like                                                   undertones.                                                      ______________________________________                                    

EXAMPLE XXIV

Four drops of one of the substances set forth in Table XIV below isadded to 1.5 grams of Aromox® to produce a clear premix. The clearpremix is added to 200 grams of CLOROX® with stirring resulting in aclear stable single phase solution. Sufficient 1 M aqueous NaOH is addedto bring the pH of the mixture up to 12.8. The solution remainssubstantially stable at 120° F. for a period of 7 days. When the 5%aqueous sodium hypochlorite solution is used as a laundry bleach, theresulting laundry on dry-out in an atmosphere of 65% relative humidityyields substantially no characteristic "hypochlorite" odor but does havea faint pleasant warm, long-lasting aroma as set forth in Table XIVbelow. Furthermore, no such characteristic "hypochlorite" aroma isretained on the hands of the individual handling such laundry in boththe wet and the dry states:

                  TABLE XIV                                                       ______________________________________                                        Structure of Compounds                                                                          Perfumery Evaluation                                        ______________________________________                                         ##STR385##       A fresh, green bean-like rosey, citrus, (petitgrain-                          like) aroma.                                                and                                                                            ##STR386##                                                                   Produced according to                                                         Example I                                                                      ##STR387##       A fruity, anisic, green aroma.                              and                                                                            ##STR388##                                                                   Produced according to                                                         Example II                                                                     ##STR389##       A green, raw potato aroma with galbanum topnotes.           and                                                                            ##STR390##                                                                   Produced according to                                                         Example III                                                                    ##STR391##       A long lasting, green, twiggy, fruity and herbaceous                          aroma.                                                      and                                                                            ##STR392##                                                                   Produced according to                                                         Example IV                                                                     ##STR393##       A sweet, fruity aroma.                                      and                                                                            ##STR394##                                                                   Produced according to                                                         Example V                                                                      ##STR395##       An excellent green aroma.                                   and                                                                            ##STR396##                                                                   Produced according to                                                         Example VI                                                                     ##STR397##       A green, sweaty aroma.                                      and                                                                            ##STR398##                                                                   Produced according to                                                         Example VII                                                                    ##STR399##       A green pea-like and green aroma.                           and                                                                            ##STR400##                                                                   Produced according to                                                         Example VIII                                                                   ##STR401##       A green and chocolate-like aroma with anther-like                             undertones                                                   ##STR402##                                                                   Produced according to                                                         Example IX                                                                     ##STR403##       A floral, green and carrot-like aroma.                      and                                                                            ##STR404##                                                                   Produced according to                                                         Example X                                                                      ##STR405##       A green, creamy, string- bean-like, herbaceous and                            floral-rosey aroma with anise-like under- tones.            and                                                                            ##STR406##                                                                   Produced according to                                                         Example XI                                                                    ______________________________________                                        Each of Examples XII (A-L) has interesting pine                               needle oil aromas with various nuances described as follows:                  Example      Aroma nuance                                                     ______________________________________                                        XII (A)      A fresh, green bean-like                                                      rosey, citrus, (petitgrain-                                                   like) aroma.                                                     XII (B)      A fruity, anisic, green aroma.                                   XII (C)      A green raw potato aroma with                                                 galbanum topnotes.                                               XII (D)      A long lasting, green, twiggy,                                                fruity and herbaceous aroma.                                     XII (E)      A sweet, fruity aroma.                                           XII (F)      An excellent green aroma.                                        XII (G)      A green, sweaty aroma.                                           XII (H)      A green pea-like and green                                                    aroma.                                                           XII (J)      A green and chocolate-like aroma                                              with anther-like undertones                                      XII (K)      A floral, green and carrot-like                                               aroma.                                                           XII (L)      A green, creamy, stringbean-                                                  like, herbaceous and floral                                                   rosey aroma with anise-like                                                   undertones.                                                      ______________________________________                                    

EXAMPLE XXV

Four drops of one of the substances set forth in Table XV below is addedto 1 gram n-undecyl dimethyl amine oxide to produce a clear premix. Theclear premix is added to 200 grams of CLOROX® with stirring resulting ina clear stable single phase solution. Sufficient 1 M aqueous NaOH isadded to bring the pH of the mixture up to 12.8. The solution remainssubstantially stable at 120° F. for a period of 7 days. When the 5%aqueous sodium hypochlorite solution is used as a laundry bleach, theresulting laundry on dry-out in an atmosphere of 65% relative humidityyields substantially no characteristic "hypochlorite" odor but does havea faint pleasant warm aroma as set forth in Table XV below. Furthermore,no such characteristic "hypochlorite" aroma is retained on the hands ofthe individual handling such laundry in both the wet and the dry states.

                  TABLE XV                                                        ______________________________________                                        Structure of Compounds                                                                          Perfumery Evaluation                                        ______________________________________                                         ##STR407##       A fresh, green bean-like, rosey, citrus, (petit-                              grain-like) aroma.                                          and                                                                            ##STR408##                                                                   Produced according to                                                         Example I                                                                      ##STR409##       A fruity, anisic, green aroma.                              and                                                                            ##STR410##                                                                   Produced according to                                                         Example II                                                                     ##STR411##       A green, raw potato aroma with galbanum topnotes.           and                                                                            ##STR412##                                                                   Produced according to                                                         Example III                                                                    ##STR413##       A long lasting, green, twiggy, fruity and herbaceous                          aroma.                                                      and                                                                            ##STR414##                                                                   Produced according to                                                         Example IV                                                                     ##STR415##       A sweet, fruity aroma.                                      and                                                                            ##STR416##                                                                   Produced according to                                                         Example V                                                                      ##STR417##       An excellent green aroma.                                   and                                                                            ##STR418##                                                                   Produced according to                                                         Example VI                                                                     ##STR419##       A green, sweaty aroma.                                      and                                                                            ##STR420##                                                                   Produced according to                                                         Example VII                                                                    ##STR421##       A green pea-like and green aroma.                           and                                                                            ##STR422##                                                                   Produced according to                                                         Example VIII                                                                   ##STR423##       A green and chocolate-like aroma with anther-like                             undertones                                                   ##STR424##                                                                   Produced according to                                                         Example IX                                                                     ##STR425##       A floral, green and carrot-like aroma.                      and                                                                            ##STR426##                                                                   Produced according to                                                         Example X                                                                      ##STR427##       A green, creamy, string- bean-like, herbaceous and                            floral-rosey aroma with anise-like under- tones.            and                                                                            ##STR428##                                                                   Produced according to                                                         Example XI                                                                    ______________________________________                                        Each of Examples XII (A-L) has interesting pine                               needle oil aromas with various nuances described as follows:                  Example      Aroma nuance                                                     ______________________________________                                        XII (A)      A fresh, green bean-like                                                      rosey, citrus, (petitgrain-                                                   like) aroma.                                                     XII (B)      A fruity, anisic, green aroma.                                   XII (C)      A green raw potato aroma with                                                 galbanum topnotes.                                               XII (D)      A long lasting, green, twiggy,                                                fruity and herbaceous aroma.                                     XII (E)      A sweet, fruity aroma.                                           XII (F)      An excellent green aroma.                                        XII (G)      A green, sweaty aroma.                                           XII (H)      A green pea-like and green                                                    aroma.                                                           XII (J)      A green and chocolate-like aroma                                              with anther-like undertones                                      XII (K)      A floral, green and carrot-like                                               aroma.                                                           XII (L)      A green, creamy, stringbean-                                                  like, herbaceous and floral-                                                  rosey aroma with anise-like                                                   undertones.                                                      ______________________________________                                    

EXAMPLE XXVI

Four drops of one of the substances as set forth in Table XVI below areadded to 1 gram of n-dedecyl dimethyl amine oxide to produce a clearpremix. The clear premix is added to 200 grams of CLOROX® with stirringresulting in a clear, stable single phase solution. Sufficient 1 Maqueous NaOH is added to bring the pH of the mixture up to 12.8. Thesolution remains substantially stable at 120° F. for a period of 7 days.When the 5% aqueous sodium hypochlorite solution is used as a laundrybleach, the resulting laundry on dry-out in an atmosphere of 65%relative humidity yields substantially no characteristic "hypochlorite"aroma, but does have a warm, pleasant, longlasting aroma as set forth inTable XVI below. Furthermore, no such characteristic "hypochlorite"aroma is retained on the hands of the individual handling such laundryin both the wet and the dry states.

                  TABLE XVI                                                       ______________________________________                                        Structure of Compounds                                                                          Perfumery Evaluation                                        ______________________________________                                         ##STR429##       A fresh, green bean-like rosey, citrus, (petit-                               grain-like) aroma.                                          and                                                                            ##STR430##                                                                    ##STR431##       A fruity, anisic, green aroma.                              and                                                                            ##STR432##                                                                   Produced according to                                                         Example II                                                                     ##STR433##       A green, raw potato aroma with galbanum topnotes.           and                                                                            ##STR434##                                                                   Produced according to                                                         Example III                                                                    ##STR435##       A long lasting, green, twiggy, fruity and herbaceous                          aroma.                                                      and                                                                            ##STR436##                                                                   Produced according to                                                         Example IV                                                                     ##STR437##       A sweet, fruity aroma.                                      and                                                                            ##STR438##                                                                   Produced according to                                                         Example V                                                                      ##STR439##       An excellent green aroma.                                   and                                                                            ##STR440##                                                                   Produced according to                                                         Example VI                                                                     ##STR441##       A green, sweaty aroma.                                      and                                                                            ##STR442##                                                                   Produced according to                                                         Example VII                                                                    ##STR443##       A green pea-like and green aroma.                           and                                                                            ##STR444##                                                                   Produced according to                                                         Example VIII                                                                   ##STR445##       A green and chocolate-like aroma with anther-like                             undertones                                                   ##STR446##                                                                   Produced according to                                                         Example IX                                                                     ##STR447##       A floral, green and carrot-like aroma.                      and                                                                            ##STR448##                                                                   Produced according to                                                         Example X                                                                      ##STR449##       A green, creamy, string- bean-like, herbaceous and                            floral-rosey aroma with anise-like under- tones.            and                                                                            ##STR450##                                                                   Produced according to                                                         Example XI                                                                    ______________________________________                                        Each of Examples XII (A-L) has interesting pine                               needle oil aromas with various nuances described as follows:                  Example      Aroma nuance                                                     ______________________________________                                        XII (A)      A fresh, green bean-like                                                      rosey, citrus, (petitgrain-                                                   like) aroma.                                                     XII (B)      A fruity, anisic, green aroma.                                   XII (C)      A green raw potato aroma with                                                 galbanum topnotes.                                               XII (D)      A long lasting, green, twiggy,                                                fruity and herbaceous aroma.                                     XII (E)      A sweet, fruity aroma.                                           XII (F)      An excellent green aroma.                                        XII (G)      A green, sweaty aroma.                                           XII (H)      A green pea-like and green                                                    aroma.                                                           XII (J)      A green and chocolate-like aroma                                              with anther-like undertones                                      XII (K)      A floral, green and carrot-like                                               aroma.                                                           XII (L)      A green, creamy, stringbean-                                                  like, herbaceous and floral                                                   rosey aroma with anise-like                                                   undertones.                                                      ______________________________________                                    

EXAMPLE XXVII

One gram of n-tridecyl dimethyl amine oxide is admixed with eight dropsof one of the substances as set forth in Table XVII below. This premixis then added with stirring to 200 grams of a 7% aqueous solution oflithium hypochlorite. Sufficient 3 M aqueous LiOH is added to bring thepH of the solution to 13.4. The mixture is then heated to 120° F. andmaintained at that temperature with stirring for a period of one week.The resulting solution remains clear in a single phase. When used as alaundry bleach, the resulting bleached laundry on dry-out in anatmosphere of 50% relative humidity retains a warm, fresh aromadescribed in Table XVII below; whereas without the use of one of thesubstances of Table XVII below, the bleached laundry has a faintcharacteristic disagreeable "hypochlorite" aroma.

                  TABLE XVII                                                      ______________________________________                                        Structure of Compounds                                                                          Perfumery Evaluation                                        ______________________________________                                         ##STR451##       A fresh, green bean-like rosey, citrus, (petit- grain)                        aroma.                                                      and                                                                            ##STR452##                                                                   Produced according to                                                         Example I                                                                      ##STR453##       A fruity, anisic, green aroma.                              and                                                                            ##STR454##                                                                   Produced according to                                                         Example II                                                                     ##STR455##       A green, raw potato aroma with galbanum topnotes.           and                                                                            ##STR456##                                                                   Produced according to                                                         Example III                                                                    ##STR457##       A long lasting, green, twiggy, fruity and herbaceous                          aroma.                                                      and                                                                            ##STR458##                                                                   Produced according to                                                         Example IV                                                                     ##STR459##       A sweet, fruity aroma.                                      and                                                                            ##STR460##                                                                   Produced according to                                                         Example V                                                                      ##STR461##       An excellent green aroma.                                   and                                                                            ##STR462##                                                                   Produced according to                                                         Example VI                                                                     ##STR463##       A green, sweaty aroma.                                      and                                                                            ##STR464##                                                                   Produced according to                                                         Example VII                                                                    ##STR465##       A green pea-like and green aroma.                           and                                                                            ##STR466##                                                                   Produced according to                                                         Example VIII                                                                   ##STR467##       A green and chocolate-like aroma with anther-like                             undertones                                                   ##STR468##                                                                   Produced according to                                                         Example IX                                                                     ##STR469##       A floral, green and carrot-like aroma.                      and                                                                            ##STR470##                                                                   Produced according to                                                         Example X                                                                      ##STR471##       A green, creamy, string- bean-like, herbaceous and                            floral-rosey aroma with anise-like under- tones.            and                                                                            ##STR472##                                                                   Produced according to                                                         Example XI                                                                    ______________________________________                                        Each of Examples XII (A-L) has interesting pine                               needle oil aromas with various nuances described as follows:                  Example      Aroma nuance                                                     ______________________________________                                        XII (A)      A fresh, green bean-like                                                      rosey, citrus, (petitgrain-                                                   like) aroma.                                                     XII (B)      A fruity, anisic, green aroma.                                   XII (C)      A green raw potato aroma with                                                 galbanum topnotes.                                               XII (D)      A long lasting, green, twiggy,                                                fruity and herbaceous aroma.                                     XII (E)      A sweet, fruity aroma.                                           XII (F)      An excellent green aroma.                                        XII (G)      A green, sweaty aroma.                                           XII (H)      A green pea-like and green                                                    aroma.                                                           XII (J)      A green and chocolate-like aroma                                              with anther-like undertones                                      XII (K)      A floral, green and carrot-like                                               aroma.                                                           XII (L)      A green, creamy, stringbean-                                                  like, herbaceous and floral-                                                  rosey aroma with anise-like                                                   undertones.                                                      ______________________________________                                    

EXAMPLE XXVIII

A "soft-feel, good-hold" hair spray is produced containing the followingingredients:

    ______________________________________                                        Ingredients         Parts by Weight                                           ______________________________________                                        Polyvinylpyrrilidones/Vinyl                                                                       4.0                                                       acetate "E-735 Copolymer                                                      manufactured by the GAF                                                       corporation of New York, N.Y.                                                 Anhydrous Ethanol   70.90                                                     Dioctyl Sebecate    0.05                                                      Benzyl Alcohol      0.05                                                      "Propellant A46" manufac-                                                                         24.95                                                     tured by the GAP corporation                                                  of New York, N.Y.                                                             Fragrance ingredient as set                                                                       0.05                                                      forth in Table XVIII below                                                    ______________________________________                                    

The PVP/VA copolymers are first dissolved in alcohol and all otheringredients are added until uniform. The propellant is then pressurizedand used as an aerosol. The resulting hairspray has a pleasant aroma asset forth in Table XVIII below:

                  TABLE XVIII                                                     ______________________________________                                        Structure of Compounds                                                                          Perfumery Evaluation                                        ______________________________________                                         ##STR473##       A fresh, green bean-like, rosey, citrus, (petit-                              grain-like) aroma.                                          and                                                                            ##STR474##                                                                   Produced according to                                                         Example I                                                                      ##STR475##       A fruity, anisic, green aroma.                              and                                                                            ##STR476##                                                                   Produced according to                                                         Example II                                                                     ##STR477##       A green, raw potato aroma with galbanum topnotes.           and                                                                            ##STR478##                                                                   Produced according to                                                         Example III                                                                    ##STR479##       A long lasting, green, twiggy, fruity and herbaceous                          aroma.                                                      and                                                                            ##STR480##                                                                   Produced according to                                                         Example IV                                                                     ##STR481##       A sweet, fruity aroma.                                      and                                                                            ##STR482##                                                                   Produced according to                                                         Example V                                                                      ##STR483##       An excellent green aroma.                                   and                                                                            ##STR484##                                                                   Produced according to                                                         Example VI                                                                     ##STR485##       A green, sweaty aroma.                                      and                                                                            ##STR486##                                                                   Produced according to                                                         Example VII                                                                    ##STR487##       A green pea-like and green aroma.                           and                                                                            ##STR488##                                                                   Produced according to                                                         Example VIII                                                                   ##STR489##       A green and chocolate-like aroma with anther-like                             undertones                                                   ##STR490##                                                                   Produced according to                                                         Example IX                                                                     ##STR491##       A floral, green and carrot-like aroma.                      and                                                                            ##STR492##                                                                   Produced according to                                                         Example X                                                                      ##STR493##       A green, creamy, string- bean-like, herbaceous and                            floral-rosey aroma with anise-like under- tones.            and                                                                            ##STR494##                                                                   Produced according to                                                         Example XI                                                                    ______________________________________                                        Each of Examples XII (A-L) has interesting pine needle                        oil aromas with various nuances described as follows:                         Example      Aroma nuance                                                     ______________________________________                                        XII (A)      A fresh, green bean-like                                                      rosey, citrus, (petitgrain-                                                   like) aroma.                                                     XII (B)      A fruity, anisic, green aroma.                                   XII (C)      A green raw potato aroma with                                                 galbanum topnotes.                                               XII (D)      A long lasting, green, twiggy,                                                fruity and herbaceous aroma.                                     XII (E)      A sweet, fruity aroma.                                           XII (F)      An excellent green aroma.                                        XII (G)      A green, sweaty aroma.                                           XII (H)      A green pea-like and green                                                    aroma.                                                           XII (J)      A green and chocolate-like aroma                                              with anther-like undertones                                      XII (K)      A floral, green and carrot-like                                               aroma.                                                           XII (L)      A green, creamy, stringbean-                                                  like, herbaceous and floral                                                   rosey aroma with anise-like                                                   undertones.                                                      ______________________________________                                    

EXAMPLE XXIX SCOURING CLEANSER COMPOSITION

A scouring cleanser composition is prepared in accordance with ExampleI, at columns 11 and 12 of U.S. Pat. No. 4,193,888, issued on Mar. 18,1980. To this composition, a substance as set forth in Table XIX belowis added at the level of 0.250% as set forth in the Table in saidExample I of U.S. Pat. No. 4,193,888 yielding an aroma on using saidcleanser in ordinary circumstances which is quite pleasant and describedin said Table XIX as set forth below:

                  TABLE XIX                                                       ______________________________________                                        Structure of Compounds                                                                          Perfumery Evaluation                                        ______________________________________                                         ##STR495##       A fresh, green bean-like rosey, citrus, (petitgrain-                          like) aroma.                                                and                                                                            ##STR496##                                                                   Produced according to                                                         Example I                                                                      ##STR497##       A fruity, anisic, green aroma.                              and                                                                            ##STR498##                                                                   Produced according to                                                         Example II                                                                     ##STR499##       A green, raw potato aroma with galbanum topnotes.           and                                                                            ##STR500##                                                                   Produced according to                                                         Example III                                                                    ##STR501##       A long lasting, green, twiggy, fruity and herbaceous                          aroma.                                                      and                                                                            ##STR502##                                                                   Produced according to                                                         Example IV                                                                     ##STR503##       A sweet, fruity aroma.                                      and                                                                            ##STR504##                                                                   Produced according to                                                         Example V                                                                      ##STR505##       An excellent green aroma.                                   and                                                                            ##STR506##                                                                   Produced according to                                                         Example VI                                                                     ##STR507##       A green, sweaty aroma.                                      and                                                                            ##STR508##                                                                   Produced according to                                                         Example VII                                                                    ##STR509##       A green pea-like and  green aroma.                          and                                                                            ##STR510##                                                                   Produced according to                                                         Example VIII                                                                   ##STR511##       A green and chocolate-like aroma with anther-like                             undertones                                                   ##STR512##                                                                   Produced according to                                                         Example IX                                                                     ##STR513##       A floral, green and carrot-like aroma.                      and                                                                            ##STR514##                                                                   Produced according to                                                         Example X                                                                      ##STR515##       A green, creamy, string- bean-like, herbaceous and                            floral-rosey aroma with anise-like under- tones.            and                                                                            ##STR516##                                                                   Produced according to                                                         Example XI                                                                    ______________________________________                                        Each of Examples XII (A-L) has interesting pine needle                        oil aromas with various nuances described as follows:                         Example      Aroma nuance                                                     ______________________________________                                        XII (A)      A fresh, green bean-like                                                      rosey, citrus, (petitgrain-                                                   like) aroma.                                                     XII (B)      A fruity, anisic, green aroma.                                   XII (C)      A green raw potato aroma with                                                 galbanum topnotes.                                               XII (D)      A long lasting, green, twiggy,                                                fruity and herbaceous aroma.                                     XII (E)      A sweet, fruity aroma.                                           XII (F)      An excellent green aroma.                                        XII (G)      A green, sweaty aroma.                                           XII (H)      A green pea-like and green                                                    aroma.                                                           XII (J)      A green and chocolate-like aroma                                              with anther-like undertones                                      XII (K)      A floral, green and carrot-like                                               aroma.                                                           XII (L)      A green, creamy, stringbean-                                                  like, herbaceous and floral-                                                  rosey aroma with anise-like                                                   undertones.                                                      ______________________________________                                    

EXAMPLE XXX

A fabric softening article prepared substantially as set forth inExample VIII of Canadian Pat. No. 1,069,260 is prepared, containing 0.21percent by weight of a perfuming substance as set forth in Table XXbelow and yielding on use in a dryer, a faint aroma as set forth inTable XX below:

                  TABLE XX                                                        ______________________________________                                        Structure of Compounds                                                                          Perfumery Evaluation                                        ______________________________________                                         ##STR517##       A fresh, green bean-like rosey, citrus, (petitgrain-                          like) aroma.                                                and                                                                            ##STR518##                                                                   Produced according to                                                         Example I                                                                      ##STR519##       A fruity, anisic, green aroma.                              and                                                                            ##STR520##                                                                   Produced according to                                                         Example II                                                                     ##STR521##       A green, raw potato aroma with galbanum topnotes.           and                                                                            ##STR522##                                                                   Produced according to                                                         Example III                                                                    ##STR523##       A long lasting, green, twiggy, fruity and herbaceous                          aroma.                                                      and                                                                            ##STR524##                                                                   Produced according to                                                         Example IV                                                                     ##STR525##       A sweet, fruity aroma.                                      and                                                                            ##STR526##                                                                   Produced according to                                                         Example V                                                                      ##STR527##       An excellent green aroma.                                   and                                                                            ##STR528##                                                                   Produced according to                                                         Example VI                                                                     ##STR529##       A green, sweaty aroma.                                      and                                                                            ##STR530##                                                                   Produced according to                                                         Example VII                                                                    ##STR531##       A green pea-like and  green aroma.                          and                                                                            ##STR532##                                                                   Produced according to                                                         Example VIII                                                                   ##STR533##       A green and chocolate-like aroma with anther-like                             undertones                                                   ##STR534##                                                                   Produced according to                                                         Example IX                                                                     ##STR535##       A floral, green and carrot-like aroma.                      and                                                                            ##STR536##                                                                   Produced according to                                                         Example X                                                                      ##STR537##       A green, creamy, string- bean-like, herbaceous and                            floral-rosey aroma with anise-like under- tones.            and                                                                            ##STR538##                                                                   Produced according to                                                         Example XI                                                                    ______________________________________                                        Each of Examples XXII (A-L) has interesting pine needle                       oil aromas with various nuances described as follows:                         Example      Aroma nuance                                                     ______________________________________                                        XII (A)      A fresh, green bean-like                                                      rosey, citrus, (petitgrain-                                                   like) aroma.                                                     XII (B)      A fruity, anisic, green aroma.                                   XII (C)      A green raw potato aroma with                                                 galbanum topnotes.                                               XII (D)      A long lasting, green, twiggy,                                                fruity and herbaceous aroma.                                     XII (E)      A sweet, fruity aroma.                                           XII (F)      An excellent green aroma.                                        XII (G)      A green, sweaty aroma.                                           XII (H)      A green pea-like and green                                                    aroma.                                                           XII (J)      A green and chocolate-like aroma                                              with anther-like undertones                                      XII (K)      A floral, green and carrot-like                                               aroma.                                                           XII (L)      A green, creamy, stringbean-                                                  like, herbaceous and floral-                                                  rosey aroma with anise-like                                                   undertones.                                                      ______________________________________                                    

What is claimed is:
 1. A process for augmenting or enhancing the aromaof a consumable material selected from the group consisting of perfumecompositions and colognes comprising the step of adding to a perfumebase or a cologne base an organoleptic property-modifying quantity of atleast one compound having a structure selected from the group consistingof: ##STR539## wherein "R" represents isopropyl; phenethyl; allyl;cyclohexyl; hydroxy alkyl or alkoxy alkyl and in each of the molecules"R" is the same.
 2. The process of claim 1 wherein the compound has thestructure: ##STR540##
 3. The process of claim 1 wherein the compound hasthe structure: ##STR541##
 4. A process for augmenting or enhancing thearoma of a consumable material selected from the group consisting ofperfume compositions and colognes comprising the step of adding to aperfume base or a cologne base an organoleptic property modifyingquantity of a product comprising a composition of matter producedaccording to a process of intimately admixing ethylidene norbornenehaving the structure: ##STR542## with an alcohol defined according tothe structure:

    R--OH

in the presence of a mineral acid catalyst or a Lewis acid catalyst andin the presence of an inert solvent or in the presence of an excess ofthe alcohol reactant, the reaction temperature varying from about 25° C.up to 120° C., the mole ratio of catalyst to ethylidene norbornenehaving the structure: ##STR543## varying from about 1:99 up to about1:10; the mole ratio of ethylidene norbornene reactant to alcohol havingthe structure:

    R--OH

reactant varying from about 1:1 up to 1:2, the moiety "R" being selectedfrom the group consisting of isopropyl; cyclohexyl; phenethyl; allyl;hydroxy alkyl and alkoxy alkyl.
 5. The process of claim 4 wherein "R" isisopropyl.